I would kind of think this goes without saying, but you don’t want to break these questions out all at once, and give your almost-guy a third degree. These are questions that you would want to just casually slip into conversation, when they actually fit, to deepen the conversation and gain a better understanding of where they are coming from. So often, someone’s past or what they want for the future will shed some light into what they’re thinking in the present. Remember not to rush it with these questions, and not to put pressure on them when asking these things. Keep a feeling of positivity and lightness, and you’ll notice how these questions get him to open up to you.

1. What was your last relationship like?

2. Do you feel like this is a time in your life where you just need to be single?

3. What was something that really turned you off from commitment?

4. What do you feel like you’re most focused on in your life right now?

5. Have you ever been cheated on?

6. Have you ever cheated on anyone?

7. Are you the kind of person who wants to bring someone home to meet your family?

8. Do you think we’ll stay friends in the future?

9. Do you feel like you might still have feelings for an ex?

10. Are you the kind of person who rebounds, or the type who is always interested in getting back into old relationships?

11. Do you consider yourself someone who is more into “just dating” or is a relationship-type person?

12. Would you want to stay in touch if we were apart for a while?

13. Do you like being accessible or do you prefer to just be off the grid?

14. Do you think love is something that comes quickly, or that builds over time?

15. What do you think of when you think of a “perfect relationship”?

16. Of your friends and your siblings relationships, whose do you actually approve of?

17. Do you think, in general, we’re too young to get into a serious relationship?

18. What was your last break up like? Were you the one who initiated it?

19. Do you think people can go from being friends to dating? Do you think it means their friendship is doomed?

20. Did you have a first love, and if so, what were they like?

21. When you need support, do you turn to other people, or do you prefer to just be there for yourself?

22. Where do you see yourself in five years?

23. What do you think your priorities will be in the future?